CN114853693A - Quaternary ammonium salt ionic liquid, preparation method thereof and application thereof as metal corrosion inhibitor - Google Patents
Quaternary ammonium salt ionic liquid, preparation method thereof and application thereof as metal corrosion inhibitor Download PDFInfo
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- CN114853693A CN114853693A CN202210733947.8A CN202210733947A CN114853693A CN 114853693 A CN114853693 A CN 114853693A CN 202210733947 A CN202210733947 A CN 202210733947A CN 114853693 A CN114853693 A CN 114853693A
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- 230000007797 corrosion Effects 0.000 title claims abstract description 67
- 238000005260 corrosion Methods 0.000 title claims abstract description 67
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 36
- 239000003112 inhibitor Substances 0.000 title claims abstract description 28
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 26
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 23
- 239000002184 metal Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 229910000861 Mg alloy Inorganic materials 0.000 claims abstract description 52
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 31
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 claims description 19
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 229960005190 phenylalanine Drugs 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229960004799 tryptophan Drugs 0.000 claims description 6
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 50
- 239000011780 sodium chloride Substances 0.000 abstract description 25
- 239000000243 solution Substances 0.000 abstract description 19
- 230000005764 inhibitory process Effects 0.000 abstract description 17
- 239000007993 MOPS buffer Substances 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 10
- 239000011777 magnesium Substances 0.000 abstract description 8
- 229910045601 alloy Inorganic materials 0.000 abstract description 6
- 239000000956 alloy Substances 0.000 abstract description 6
- 238000005536 corrosion prevention Methods 0.000 abstract description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 229910052749 magnesium Inorganic materials 0.000 abstract description 2
- 238000002791 soaking Methods 0.000 abstract 1
- 238000001878 scanning electron micrograph Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 17
- 239000000523 sample Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- -1 quaternary ammonium salt cations Chemical class 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 244000137852 Petrea volubilis Species 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000000840 electrochemical analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
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- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
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- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/141—Amines; Quaternary ammonium compounds
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- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
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- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
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- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/145—Amides; N-substituted amides
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- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
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- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/16—Sulfur-containing compounds
- C23F11/163—Sulfonic acids
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Abstract
The invention discloses three quaternary ammonium salt ionic liquids, the molecular structural formula of which is as follows:
Description
Technical Field
The invention belongs to the technical field of ionic liquids, and particularly relates to a quaternary ammonium salt ionic liquid, a preparation method and application thereof as a metal corrosion inhibitor, especially a magnesium alloy corrosion inhibitor.
Background
The magnesium alloy has ideal physical properties, and has the advantages of low density, good specific property, good damping property, good electric and heat conductivity, good processing property and the like. The properties enable the magnesium alloy to have wide application prospects in the fields of aerospace, transportation, electronic industry and medical treatment. However, magnesium alloys have low standard potential, high chemical activity, and poor corrosion resistance, and even in industrial atmosphere and marine atmosphere environments, they are severely corroded, and thus their applications are greatly limited. Therefore, how to solve the corrosion problem of magnesium alloys becomes a key factor for the wide application of magnesium alloys in various fields. The corrosion inhibitor is added, so that the corrosion inhibition method has strong applicability, can effectively inhibit metal corrosion by using the corrosion inhibitor, and plays a significant role in protecting resources and reducing material loss.
Corrosion inhibitors are chemicals or compounds that are present in corrosive media in a suitable concentration and form to effectively slow the corrosion of metals and their alloys. Compared with other anticorrosion technologies, the corrosion inhibitor has the advantages of easy operation, simple equipment, low cost, high efficiency and the like. Due to its good performance and high yield, corrosion inhibitors have been widely used in many fields related to metal corrosion protection in production and life.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, solve the problems of corrosion of metal magnesium and alloy thereof and the like, and provide the quaternary ammonium salt ionic liquid with good corrosion inhibition performance, high efficiency and economy.
The invention also provides a simple preparation method of the quaternary ammonium salt ionic liquid and application of the quaternary ammonium salt ionic liquid as a metal corrosion inhibitor, in particular to a magnesium alloy corrosion inhibitor.
In order to achieve the purpose, the invention adopts the following technical scheme:
a quaternary ammonium salt ionic liquid ([ DMBAB ] [ MOPS ], [ DMBAB ] [ Phe ], [ DMBAB ] [ Trp ]), the molecular structural formula of which is shown in any one of the following formulas:
the invention provides a preparation method of the quaternary ammonium salt ionic liquid, which comprises the following steps:
1) reacting biphenyl dichlorobenzyl with N, N-dimethylbenzylamine at the temperature of 110 ℃ for 16 +/-4 hours in the presence of a solvent of toluene and inert gas (such as argon, nitrogen and the like) to obtain [ DMBAB ] [ Cl ];
2) in the presence of ethanol serving as a solvent, reacting [ DMBAB ] [ Cl ] with KOH at 25 +/-5 ℃ for 6 +/-2 hours to obtain [ DMBAB ] [ OH ];
3) in the presence of solvent ethanol, [ DMBAB ] [ OH ] reacts with 3-morpholine propanesulfonic acid, L-phenylalanine or L-tryptophan at 50 +/-5 ℃ for 12 +/-4 h to carry out anion exchange, and quaternary ammonium salt ionic liquids [ DMBAB ] [ MOPS ], [ DMBAB ] [ Phe ] and [ DMBAB ] [ Trp ] are obtained.
Specifically, in the step 1), the mass ratio of the biphenyl dichlorobenzyl to the N, N-dimethylbenzylamine is 1:2-3, preferably 1: 2.4.
Specifically, in step 2), the mass ratio of [ DMBAB ] [ Cl ] to KOH is 1:2.
Further, in step 3), the ratio of [ DMBAB ] [ OH ] to the amount of the substance of 3-morpholinopropanesulfonic acid, L-phenylalanine or L-tryptophan is 1:2. According to the reaction formula, the molar amount of [ DMBAB ] [ OH ] produced is the same as that of the starting material [ DMBAB ] [ Cl ], and therefore it can also be said that the ratio of [ DMBAB ] [ Cl ] to the amount of the substance of 3-morpholinopropanesulfonic acid, L-phenylalanine or L-tryptophan is 1:2.
The invention also provides application of the quaternary ammonium salt ionic liquid as a metal corrosion inhibitor.
Further, the quaternary ammonium salt ionic liquid is used as a metal corrosion inhibitor, and the metal is preferably magnesium alloy.
The three quaternary ammonium salt ionic liquids have obvious effect on corrosion prevention of magnesium alloy, and specifically comprise the following components:
(1) electrochemical tests show that: the three ionic liquids [ DMBAB ] [ MOPS ], [ DMBAB ] [ Phe ] and [ DMBAB ] [ Trp ] have good corrosion inhibition effect on the magnesium alloy, the [ DMBAB ] [ Trp ] with the concentration of 0.7mM has the best corrosion inhibition effect on the magnesium alloy in 0.5 wt.% of NaCl medium, and the corrosion inhibition efficiency is 88.8%;
(2) AZ91D Mg alloy was soaked in 0.5 wt.% NaCl and [ DMBAB ] [ MOPS ], [ DMBAB ] [ Phe ], [ DMBAB ] [ Trp ] corrosion inhibitor solution formulated with 0.5 wt.% NaCl at a concentration of 0.3 mM, 0.5 mM, 0.7mM for 10 h. In contrast to the blank sample, it can be seen by some morphological characterization means that: the three ionic liquids have good corrosion inhibition effect on the magnesium alloy, and the surface of the magnesium alloy soaked in 0.7mM of DMBAB Phe solution is the smoothest, and the corrosion inhibition effect is the best.
According to the invention, quaternary ammonium salt cations and three organic acid anions are combined together to form macromolecules with relative molecular masses of 867, 779 and 857 respectively, so that the quaternary ammonium salt cations can cover more metal surfaces, and the adsorption capacity of the corrosion inhibitor on the metal surfaces is improved. The molecule contains N, O, S heteroatoms and conjugated groups, which can react with the alloy and adsorb onto the surface of magnesium alloy, thus playing the role of corrosion protection. Based on the above, the technology of using the magnesium alloy as a corrosion inhibitor to slow down the corrosion speed of the magnesium alloy is determined. Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the [ DMBAB ] [ MOPS ], [ DMBAB ] [ Phe ], [ DMBAB ] [ Trp ] ionic liquid has the advantages of low raw material price, simple synthesis method, mild reaction conditions, no need of complex post-treatment and the like;
(2) the [ DMBAB ] [ MOPS ], [ DMBAB ] [ Phe ], [ DMBAB ] [ Trp ] ionic liquid contains N, O, S heteroatom and conjugated group, is easy to interact with metal, and forms a film layer between the surface of the metal and alloy and a corrosive medium;
(3) the three ionic liquid corrosion inhibitors are macromolecules with the relative molecular masses of 867, 779 and 857 respectively, can better cover the metal surface, have the advantages of high efficiency, economy and the like, improve the adsorption capacity of corrosion inhibitor molecules on the metal surface, and have good prospects in the aspect of corrosion inhibition application of magnesium alloys.
Drawings
FIG. 1 shows SEM images of AZ91D Mg blocks under different conditions, wherein a is the SEM image of an AZ91D Mg alloy sample after being placed in 0.5 wt.% NaCl medium for 10 h; b is an SEM image of a sample of AZ91D Mg alloy after 10 h in a solution containing 0.5 wt.% NaCl medium and 0.5 mM [ DMBAB ] [ MOPS ]; c is an SEM image of a sample of AZ91D Mg alloy after 10 h in a solution containing 0.5 wt.% NaCl medium and 0.5 mM [ DMBAB ] [ Phe ]; d is an SEM image of a sample of AZ91D Mg alloy after 10 h in a solution containing 0.5 wt.% NaCl medium and 0.7mM [ DMBAB ] [ Trp ];
FIG. 2 shows SEM images of AZ91D Mg blocks after cleaning of corrosion products under different conditions, wherein a is the SEM image of an AZ91D Mg alloy sample after being placed in a 0.5 wt.% NaCl medium for 10 h; b is an SEM image of a sample of AZ91D Mg alloy after being placed in a solution containing 0.5 wt.% NaCl medium and 0.5 mM [ DMBAB ] [ MOPS ] for 10 h and cleaned of corrosion products; c is an SEM image of a sample of AZ91D Mg alloy after washing the corrosion products by placing it in a solution containing 0.5 wt.% NaCl medium and 0.5 mM [ DMBAB ] [ Phe ]; d is the SEM image after the corrosion product was cleaned by placing a sample of AZ91D Mg alloy in a solution containing 0.5 wt.% NaCl medium and 0.7mM [ DMBAB ] [ Trp ] for 10 h.
Detailed Description
The technical solution of the present invention is further described in detail with reference to the following examples, but the scope of the present invention is not limited thereto.
The raw materials used are all common commercial products which can be directly purchased, unless otherwise specified below.
Example 1:
the preparation method of the quaternary ammonium salt ionic liquid 3-morpholine propanesulfonic acid dimethylbenzyl-1, 1' -bi-p-tolyl ammonium [ DMBAB ] [ MOPS ] comprises the following steps:
(1) in a three-necked flask, 5.02 g (20 mmol) of biphenyldichlorobenzyl, 200 mL of toluene as a solvent, and 7.82 g (48 mmol) of N, N-dimethylbenzylamine were charged and reacted at 100 ℃ for 16 hours under a nitrogen atmosphere. The solvent was distilled off under reduced pressure at 70 ℃ and washed three times with ethyl acetate to give the product [ DMBAB ] [ Cl ] (yield 95%) as a white solid;
(2) 5.21 g (10 mmol) of the product [ DMBAB ] [ Cl ] of step (1) was taken in a round-bottomed flask, 100 mL of ethanol was added as a solvent, 1.12 g (20 mmol) of KOH was added, and the mixture was reacted at 25 ℃ for 6 hours. The KCl was subsequently removed by vacuum filtration separation, and the procedure was repeated three times to ensure the purity of the final product;
(3) to the solution obtained in step (2), 4.18 g (20 mmol) of 3-morpholinopropanesulfonic acid was added and reacted at 50 ℃ for 12 hours. By distillation at 40 ℃ under reduced pressure, a viscous liquid was obtained. The product was further dried in a vacuum oven at 60 ℃ for 24 h. The obtained light yellow viscous liquid is [ DMBAB ] [ MOPS ] ionic liquid (yield: 92.0%); the map information is as follows:
1 H NMR (400 MHz, DMSO-d6) δ: 7.91 (d, J = 7.9 Hz, 4H), 7.72 (d, J = 7.9 Hz, 4H), 7.65~7.51 (m, 10H), 4.65 (d, J = 10.4 Hz, 8H), 3.56 (s, 8H), 2.91 (s, 12H), 2.38 (d, J= 37.3 Hz, 16H), 1.73 (s, 4H); the structural formula is as follows:
example 2:
the preparation method of the quaternary ammonium salt ionic liquid L-phenylalanine dimethylbenzyl-1, 1' -di-p-tolyl ammonium [ DMBAB ] [ Phe ] comprises the following steps:
(1) same as example 1, step (1);
(2) same as example 1, step (2);
(3) to the solution obtained in step (2), 3.30 g (20 mmol) of L-phenylalanine was added, reacted at 50 ℃ for 12 hours, and concentrated by rotary evaporation to obtain a viscous liquid. The product was dried in a vacuum oven at 60 ℃ for 24 h. The obtained light yellow viscous liquid is [ DMBAB ] [ Phe ] ionic liquid (yield: 94.5%); the map information is as follows:
1 H NMR (400 MHz, Methanol-d 4 ) δ: 7.87 (d, J = 8.1 Hz, 4H), 7.71 (d, J= 8.0 Hz, 4H), 7.58 (q, J = 5.7, 4.9 Hz, 10H), 7.30~7.22 (m, 10H), 4.64 (dd, J = 10.0, 6.8 Hz, 8H), 3.56 (dd, J = 8.4, 4.5 Hz, 2H), 3.18 (dd, J = 13.9, 4.6 Hz, 2H), 2.97 (s, J = 4.2 Hz, 12H), 2.84 (dd, J= 13.8, 8.5 Hz, 2H). The structural formula is as follows:
example 3:
the preparation method of the quaternary ammonium salt ionic liquid L-tryptophan dimethylbenzyl-1, 1' -di-p-tolyl ammonium [ DMBAB ] [ Trp ] comprises the following steps:
(1) same as example 1, step (1);
(2) same as example 1, step (2);
(3) to the solution obtained in step (2) was added 4.10g (20 mmol) of L-tryptophan, reacted at 50 ℃ for 12 hours, and concentrated by rotary evaporation to give a viscous liquid. The product was further dried in a vacuum oven at 60 ℃ for 24 h. The obtained dark brown solid is [ DMBAB ] [ Trp ] ionic liquid (yield: 91.40%); the map information is as follows:
1 H NMR (300 MHz, DMSO-d 6 ) δ: 7.87 (d, J = 8.0 Hz, 4H), 7.73 (d, J = 8.1 Hz, 4H), 7.66~7.60 (m, 4H), 7.53 (q, J = 6.1 Hz, 8H), 7.33 (d, J = 8.0 Hz, 2H), 7.19 – 7.15 (m, 2H), 7.05~6.98 (m, 2H), 6.92 (t, J = 7.4 Hz, 2H), 4.72 (d, J = 10.0 Hz, 8H), 3.45 (d, J= 7.0 Hz, 2H), 2.90 (s, 12H). The structural formula is as follows:
application test 1 shows that the corrosion inhibitors [ DMBAB ] [ MOPS ], [ DMBAB ] [ Phe ], [ DMBAB ] [ Trp ] have corrosion inhibition performance on AZ91D Mg alloy in 0.5 wt.% NaCl medium
Different concentrations of [ DMBAB were formulated in 0.5 wt.% NaCl medium][MOPS]、[DMBAB][Phe]And [ DMBAB ]][Trp](see table 1), Mg alloys were tested using the CHI650E electrochemical workstation, electrochemical tests were performed under a three-electrode system with a saturated calomel electrode as the reference electrode (SCE), a platinum electrode as the Counter Electrode (CE), and an AZ91D magnesium alloy as the Working Electrode (WE). AZ91D Mg (composition: 7.19 wt.% Al, 0.67 wt.% Zn, 0.3 wt.% Mn, 0.001 wt.% Cu,<0.001 wt.％ Fe，<0.01 wt.% Ca, balance Mg) size of 1.00 cm x 0.50 cm. At the same time, the electrochemical sample was embedded in epoxy resin, leaving only 1.00 cm of exposure to the test solution 2 One side of (a). Prior to all experiments, the working surface was previously subjected to the following treatments: mechanically polishing by using sand paper (metallographic sand paper: 180-. All samples were tested within 1 h.
Table 1 shows the impedance efficiency measured at various concentrations of [ DMBAB ] [ MOPS ], [ DMBAB ] [ Phe ], [ DMBAB ] [ Trp ]. As can be seen from table 1: under 0.5 wt.% NaCl, corrosion inhibitors with different concentrations have the corrosion inhibition efficiency of 66-88% on AZ91D Mg alloy, 0.7mM [ DMBAB ] [ Trp ] has the best corrosion inhibition effect on magnesium alloy in 0.5 wt.% NaCl medium, and the corrosion inhibition efficiency is 88.8%.
TABLE 1 Corrosion inhibition efficiency (%)% of various concentrations of corrosion inhibitors on AZ91D Mg alloy at 0.5 wt.% NaCl
Fig. 1 shows SEM images of AZ91D Mg blocks under different conditions, wherein a in fig. 1 is an SEM image of an AZ91D Mg alloy sample after being placed in 0.5 wt.% NaCl medium for 10 h; FIG. 1, b is an SEM image of a sample of AZ91D Mg alloy after 10 h in a solution containing 0.5 wt.% NaCl medium and 0.5 mM [ DMBAB ] [ MOPS ]; FIG. 1c is a SEM image of a sample of AZ91D Mg alloy after 10 h in a solution containing 0.5 wt.% NaCl medium and 0.5 mM [ DMBAB ] [ Phe ]; FIG. 1d is an SEM image of a sample of AZ91D Mg alloy after 10 h in a solution containing 0.5 wt.% NaCl medium and 0.7mM [ DMBAB ] [ Trp ]. By comparing SEM images of a-d in FIG. 1, it is found that: the corrosion products on the surface of the magnesium alloy of fig. 1 b-d added with the corrosion inhibitor are less, wherein the surface film layer of the magnesium alloy of fig. 1c is the most compact and the corrosion products are the least. The corrosion inhibitor plays a good role in corrosion protection on AZ91 Mg alloy, wherein the corrosion prevention effect of the DMBAB (Phe) is the best after the alloy is soaked for a period of time.
FIG. 2 shows SEM images of AZ91D Mg after cleaning corrosion products under different conditions, wherein a in FIG. 2 is the SEM image of an AZ91D Mg alloy sample after being placed in a 0.5 wt.% NaCl medium for 10 h and cleaned corrosion products; FIG. 2b is an SEM image of a sample of AZ91D Mg alloy after washing the corrosion products by placing it in a solution containing 0.5 wt.% NaCl medium and 0.5 mM [ DMBAB ] [ MOPS ]; FIG. 2c is a SEM image of a sample of AZ91D Mg alloy after washing the corrosion products by placing it in a solution containing 0.5 wt.% NaCl medium and 0.5 mM [ DMBAB ] [ Phe ]; FIG. 2 d is an SEM image of a sample of AZ91D Mg alloy after washing the corrosion products by placing it in a solution containing 0.5 wt.% NaCl medium and 0.7mM [ DMBAB ] [ Trp ] for 10 h. By comparing SEM images of a-d in FIG. 2, it is found that: the magnesium alloy in FIGS. 2 b-d has fewer corrosion pits and smoother surface, with the magnesium alloy in FIG. 2c having the smoothest surface.
In conclusion, the three ionic liquid corrosion inhibitors can better cover the surface of metal, particularly magnesium alloy, improve the adsorption capacity of corrosion inhibitor molecules on the surface of the metal, and simultaneously form a compact film layer on the surface of the magnesium alloy, thereby achieving good corrosion inhibition effect and having good prospect in the aspect of corrosion inhibition application of the magnesium alloy.
Finally, it should be noted that: although the present invention has been described in detail with reference to the above embodiments, it should be understood by those skilled in the art that: modifications and equivalents may be made thereto without departing from the spirit and scope of the invention and it is intended to cover in the claims the invention as defined in the appended claims.
Claims (7)
1. The quaternary ammonium salt ionic liquid is characterized in that the molecular structural formula is shown as any one of the following formulas:
2. the method for preparing the quaternary ammonium salt ionic liquid according to claim 1, which is characterized by comprising the following steps:
1) reacting biphenyl dichlorobenzyl with N, N-dimethylbenzylamine at the temperature of 110 ℃ for 16 +/-4 hours in the presence of a solvent of toluene and inert gas to obtain [ DMBAB ] [ Cl ];
2) in the presence of ethanol serving as a solvent, reacting [ DMBAB ] [ Cl ] with KOH at 25 +/-5 ℃ for 6 +/-2 hours to obtain [ DMBAB ] [ OH ];
3) in the presence of ethanol as a solvent, reacting [ DMBAB ] [ OH ] with 3-morpholine propanesulfonic acid, L-phenylalanine or L-tryptophan at 50 +/-5 ℃ for 12 +/-4 h to obtain the quaternary ammonium salt ionic liquid.
3. The method for preparing the quaternary ammonium salt ionic liquid according to claim 2, wherein the mass ratio of the biphenyl dichlorobenzyl to the N, N-dimethylbenzylamine in the step 1) is 1: 2-3.
4. The method for preparing the quaternary ammonium salt ionic liquid according to claim 1, wherein in the step 2), the mass ratio of the substances of [ DMBAB ] [ Cl ] to KOH is 1:2.
5. The method for preparing the quaternary ammonium salt ionic liquid according to claim 1, wherein in the step 3), the ratio of the amount of the substance of [ DMBAB ] [ OH ] to the amount of the substance of 3-morpholinopropanesulfonic acid, L-phenylalanine or L-tryptophan is 1:2.
6. The use of the quaternary ammonium salt ionic liquid of claim 1 as a metal corrosion inhibitor.
7. The use of the quaternary ammonium salt ionic liquid of claim 6 as a metal corrosion inhibitor, wherein the metal is a magnesium alloy.
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